US2179196A - Manufacture of artificial silk - Google Patents
Manufacture of artificial silk Download PDFInfo
- Publication number
- US2179196A US2179196A US212187A US21218738A US2179196A US 2179196 A US2179196 A US 2179196A US 212187 A US212187 A US 212187A US 21218738 A US21218738 A US 21218738A US 2179196 A US2179196 A US 2179196A
- Authority
- US
- United States
- Prior art keywords
- compounds
- spinning
- cation
- radicals
- radical
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 238000004519 manufacturing process Methods 0.000 title description 8
- 229920002955 Art silk Polymers 0.000 title 1
- 150000001875 compounds Chemical class 0.000 description 40
- 238000009987 spinning Methods 0.000 description 35
- 150000003254 radicals Chemical class 0.000 description 33
- 125000004429 atom Chemical group 0.000 description 26
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 22
- 150000001768 cations Chemical class 0.000 description 21
- 229920000297 Rayon Polymers 0.000 description 19
- 230000000694 effects Effects 0.000 description 19
- 150000001450 anions Chemical class 0.000 description 17
- -1 heterocyclic radicals Chemical class 0.000 description 17
- 229910052757 nitrogen Inorganic materials 0.000 description 13
- 150000003839 salts Chemical class 0.000 description 13
- 239000002585 base Substances 0.000 description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 230000001939 inductive effect Effects 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 125000001931 aliphatic group Chemical group 0.000 description 7
- 125000002837 carbocyclic group Chemical group 0.000 description 7
- 229940107816 ammonium iodide Drugs 0.000 description 6
- SVZIAFPYRMWMCG-UHFFFAOYSA-N 4-(trimethylammonium)benzenediazonium Chemical compound C[N+](C)(C)C1=CC=C([N+]#N)C=C1 SVZIAFPYRMWMCG-UHFFFAOYSA-N 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 5
- 239000005864 Sulphur Substances 0.000 description 5
- 238000007792 addition Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 229910021653 sulphate ion Inorganic materials 0.000 description 5
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 229910052785 arsenic Inorganic materials 0.000 description 4
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 229910052698 phosphorus Inorganic materials 0.000 description 4
- 239000011574 phosphorus Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 229920002678 cellulose Polymers 0.000 description 3
- 239000001913 cellulose Substances 0.000 description 3
- USEXUESVOVNRHP-UHFFFAOYSA-M dodecyl(triethyl)azanium;iodide Chemical compound [I-].CCCCCCCCCCCC[N+](CC)(CC)CC USEXUESVOVNRHP-UHFFFAOYSA-M 0.000 description 3
- BBKFSSMUWOMYPI-UHFFFAOYSA-N gold palladium Chemical compound [Pd].[Au] BBKFSSMUWOMYPI-UHFFFAOYSA-N 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- VUEDNLCYHKSELL-UHFFFAOYSA-N arsonium Chemical compound [AsH4+] VUEDNLCYHKSELL-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-M bisulphate group Chemical group S([O-])(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 238000001125 extrusion Methods 0.000 description 2
- 239000010437 gem Substances 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 229940112041 peripherally acting muscle relaxants other quaternary ammonium compound in atc Drugs 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 2
- 230000001376 precipitating effect Effects 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 2
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 2
- 235000009529 zinc sulphate Nutrition 0.000 description 2
- 239000011686 zinc sulphate Substances 0.000 description 2
- FFYRIXSGFSWFAQ-UHFFFAOYSA-N 1-dodecylpyridin-1-ium Chemical group CCCCCCCCCCCC[N+]1=CC=CC=C1 FFYRIXSGFSWFAQ-UHFFFAOYSA-N 0.000 description 1
- GKQHIYSTBXDYNQ-UHFFFAOYSA-M 1-dodecylpyridin-1-ium;chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+]1=CC=CC=C1 GKQHIYSTBXDYNQ-UHFFFAOYSA-M 0.000 description 1
- IQDVXXOBJULTFE-UHFFFAOYSA-M 1-dodecylpyridin-1-ium;hydron;sulfate Chemical compound OS([O-])(=O)=O.CCCCCCCCCCCC[N+]1=CC=CC=C1 IQDVXXOBJULTFE-UHFFFAOYSA-M 0.000 description 1
- GZNACENTEXAZDR-UHFFFAOYSA-M 1-dodecylpyridin-1-ium;iodide Chemical compound [I-].CCCCCCCCCCCC[N+]1=CC=CC=C1 GZNACENTEXAZDR-UHFFFAOYSA-M 0.000 description 1
- KQVYBYSUVFRMGE-UHFFFAOYSA-M 1-hexadecylpyridin-1-ium;iodide Chemical compound [I-].CCCCCCCCCCCCCCCC[N+]1=CC=CC=C1 KQVYBYSUVFRMGE-UHFFFAOYSA-M 0.000 description 1
- JDASKPRUFDKACZ-UHFFFAOYSA-M 1-octadecylpyridin-1-ium;bromide Chemical compound [Br-].CCCCCCCCCCCCCCCCCC[N+]1=CC=CC=C1 JDASKPRUFDKACZ-UHFFFAOYSA-M 0.000 description 1
- XDCILYQINRVJBM-UHFFFAOYSA-M 1-octylpyridin-1-ium;iodide Chemical compound [I-].CCCCCCCC[N+]1=CC=CC=C1 XDCILYQINRVJBM-UHFFFAOYSA-M 0.000 description 1
- XZXYQEHISUMZAT-UHFFFAOYSA-N 2-[(2-hydroxy-5-methylphenyl)methyl]-4-methylphenol Chemical compound CC1=CC=C(O)C(CC=2C(=CC=C(C)C=2)O)=C1 XZXYQEHISUMZAT-UHFFFAOYSA-N 0.000 description 1
- IEZDTNCUMWPRTD-UHFFFAOYSA-N 346704-04-9 Chemical compound [O-][N+](=O)C1=CC=C(N2CCNCC2)C=C1N1CCCCC1 IEZDTNCUMWPRTD-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- UZIQYAYUUNMDMU-UHFFFAOYSA-N N.[Br+] Chemical compound N.[Br+] UZIQYAYUUNMDMU-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- YRCOEIBVPXHKSP-UHFFFAOYSA-M [Br-].C(CC)[S+](CCCCCCCCCCCC)CCC Chemical compound [Br-].C(CC)[S+](CCCCCCCCCCCC)CCC YRCOEIBVPXHKSP-UHFFFAOYSA-M 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000003868 ammonium compounds Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 239000001166 ammonium sulphate Substances 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 229940027983 antiseptic and disinfectant quaternary ammonium compound Drugs 0.000 description 1
- IKADZPYEPSHGPY-UHFFFAOYSA-N benzene;n,n-dimethylmethanamine Chemical compound CN(C)C.C1=CC=CC=C1 IKADZPYEPSHGPY-UHFFFAOYSA-N 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 230000001112 coagulating effect Effects 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- GLMVLQYWBUDYMM-UHFFFAOYSA-M decyl(triethyl)azanium;iodide Chemical compound [I-].CCCCCCCCCC[N+](CC)(CC)CC GLMVLQYWBUDYMM-UHFFFAOYSA-M 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- ZNRGDYAGUTWXOZ-UHFFFAOYSA-M dimethyl-(2-methylpropyl)-naphthalen-1-ylazanium iodide Chemical compound [I-].C(C)(C)C[N+](C)(C)C1=CC=CC2=CC=CC=C12 ZNRGDYAGUTWXOZ-UHFFFAOYSA-M 0.000 description 1
- 230000003292 diminished effect Effects 0.000 description 1
- GDNCXORZAMVMIW-UHFFFAOYSA-N dodecane Chemical compound [CH2]CCCCCCCCCCC GDNCXORZAMVMIW-UHFFFAOYSA-N 0.000 description 1
- YPEJOAFIHQTUGB-UHFFFAOYSA-M dodecyl(diethyl)sulfanium;hydroxide Chemical compound [OH-].CCCCCCCCCCCC[S+](CC)CC YPEJOAFIHQTUGB-UHFFFAOYSA-M 0.000 description 1
- FGZITYYQBBOYGD-UHFFFAOYSA-L dodecyl(triethyl)azanium;sulfate Chemical compound [O-]S([O-])(=O)=O.CCCCCCCCCCCC[N+](CC)(CC)CC.CCCCCCCCCCCC[N+](CC)(CC)CC FGZITYYQBBOYGD-UHFFFAOYSA-L 0.000 description 1
- VWCVFZYCPINDQW-UHFFFAOYSA-M dodecyl(trimethyl)phosphanium;hydroxide Chemical compound [OH-].CCCCCCCCCCCC[P+](C)(C)C VWCVFZYCPINDQW-UHFFFAOYSA-M 0.000 description 1
- XJWSAJYUBXQQDR-UHFFFAOYSA-M dodecyltrimethylammonium bromide Chemical compound [Br-].CCCCCCCCCCCC[N+](C)(C)C XJWSAJYUBXQQDR-UHFFFAOYSA-M 0.000 description 1
- ZOOODBUHSVUZEM-UHFFFAOYSA-N ethoxymethanedithioic acid Chemical compound CCOC(S)=S ZOOODBUHSVUZEM-UHFFFAOYSA-N 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- JUWSSMXCCAMYGX-UHFFFAOYSA-N gold platinum Chemical compound [Pt].[Au] JUWSSMXCCAMYGX-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical compound [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical group CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- DJFBJKSMACBYBD-UHFFFAOYSA-N phosphane;hydrate Chemical compound O.P DJFBJKSMACBYBD-UHFFFAOYSA-N 0.000 description 1
- PMOIAJVKYNVHQE-UHFFFAOYSA-N phosphanium;bromide Chemical compound [PH4+].[Br-] PMOIAJVKYNVHQE-UHFFFAOYSA-N 0.000 description 1
- 239000010970 precious metal Substances 0.000 description 1
- BBFCIBZLAVOLCF-UHFFFAOYSA-N pyridin-1-ium;bromide Chemical compound Br.C1=CC=NC=C1 BBFCIBZLAVOLCF-UHFFFAOYSA-N 0.000 description 1
- QYPWRPSMKLUGJZ-UHFFFAOYSA-N pyridin-1-ium;sulfate Chemical compound [O-]S([O-])(=O)=O.C1=CC=[NH+]C=C1.C1=CC=[NH+]C=C1 QYPWRPSMKLUGJZ-UHFFFAOYSA-N 0.000 description 1
- OENLEHTYJXMVBG-UHFFFAOYSA-N pyridine;hydrate Chemical compound [OH-].C1=CC=[NH+]C=C1 OENLEHTYJXMVBG-UHFFFAOYSA-N 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000010979 ruby Substances 0.000 description 1
- 229910001750 ruby Inorganic materials 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- SSTZGACKDAVIGZ-UHFFFAOYSA-N sulfanium;bromide Chemical compound [SH3+].[Br-] SSTZGACKDAVIGZ-UHFFFAOYSA-N 0.000 description 1
- RVEZZJVBDQCTEF-UHFFFAOYSA-N sulfenic acid Chemical compound SO RVEZZJVBDQCTEF-UHFFFAOYSA-N 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000011009 synthetic ruby Substances 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
- 125000005207 tetraalkylammonium group Chemical group 0.000 description 1
- 150000005621 tetraalkylammonium salts Chemical class 0.000 description 1
- QFGWYYQGDCVPFQ-UHFFFAOYSA-M triethyl(hexadecyl)azanium;iodide Chemical compound [I-].CCCCCCCCCCCCCCCC[N+](CC)(CC)CC QFGWYYQGDCVPFQ-UHFFFAOYSA-M 0.000 description 1
- QSDPPNNSYMTIKB-UHFFFAOYSA-M triethyl(octyl)azanium;iodide Chemical compound [I-].CCCCCCCC[N+](CC)(CC)CC QSDPPNNSYMTIKB-UHFFFAOYSA-M 0.000 description 1
- 239000012991 xanthate Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/02—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
- C08J3/09—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in organic liquids
- C08J3/091—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in organic liquids characterised by the chemical constitution of the organic liquid
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B23—MACHINE TOOLS; METAL-WORKING NOT OTHERWISE PROVIDED FOR
- B23K—SOLDERING OR UNSOLDERING; WELDING; CLADDING OR PLATING BY SOLDERING OR WELDING; CUTTING BY APPLYING HEAT LOCALLY, e.g. FLAME CUTTING; WORKING BY LASER BEAM
- B23K35/00—Rods, electrodes, materials, or media, for use in soldering, welding, or cutting
- B23K35/40—Making wire or rods for soldering or welding
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29B—PREPARATION OR PRETREATMENT OF THE MATERIAL TO BE SHAPED; MAKING GRANULES OR PREFORMS; RECOVERY OF PLASTICS OR OTHER CONSTITUENTS OF WASTE MATERIAL CONTAINING PLASTICS
- B29B13/00—Conditioning or physical treatment of the material to be shaped
- B29B13/06—Conditioning or physical treatment of the material to be shaped by drying
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B65—CONVEYING; PACKING; STORING; HANDLING THIN OR FILAMENTARY MATERIAL
- B65D—CONTAINERS FOR STORAGE OR TRANSPORT OF ARTICLES OR MATERIALS, e.g. BAGS, BARRELS, BOTTLES, BOXES, CANS, CARTONS, CRATES, DRUMS, JARS, TANKS, HOPPERS, FORWARDING CONTAINERS; ACCESSORIES, CLOSURES, OR FITTINGS THEREFOR; PACKAGING ELEMENTS; PACKAGES
- B65D71/00—Bundles of articles held together by packaging elements for convenience of storage or transport, e.g. portable segregating carrier for plural receptacles such as beer cans or pop bottles; Bales of material
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
-
- D—TEXTILES; PAPER
- D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
- D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
- D01F2/00—Monocomponent artificial filaments or the like of cellulose or cellulose derivatives; Manufacture thereof
- D01F2/06—Monocomponent artificial filaments or the like of cellulose or cellulose derivatives; Manufacture thereof from viscose
- D01F2/08—Composition of the spinning solution or the bath
-
- D—TEXTILES; PAPER
- D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
- D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
- D01F2/00—Monocomponent artificial filaments or the like of cellulose or cellulose derivatives; Manufacture thereof
- D01F2/06—Monocomponent artificial filaments or the like of cellulose or cellulose derivatives; Manufacture thereof from viscose
- D01F2/08—Composition of the spinning solution or the bath
- D01F2/10—Addition to the spinning solution or spinning bath of substances which exert their effect equally well in either
-
- D—TEXTILES; PAPER
- D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
- D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
- D01F6/00—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof
- D01F6/02—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolymers obtained by reactions only involving carbon-to-carbon unsaturated bonds
- D01F6/18—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolymers obtained by reactions only involving carbon-to-carbon unsaturated bonds from polymers of unsaturated nitriles, e.g. polyacrylonitrile, polyvinylidene cyanide
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F26—DRYING
- F26B—DRYING SOLID MATERIALS OR OBJECTS BY REMOVING LIQUID THEREFROM
- F26B21/00—Arrangements or duct systems, e.g. in combination with pallet boxes, for supplying and controlling air or gases for drying solid materials or objects
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F26—DRYING
- F26B—DRYING SOLID MATERIALS OR OBJECTS BY REMOVING LIQUID THEREFROM
- F26B23/00—Heating arrangements
- F26B23/02—Heating arrangements using combustion heating
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01R—ELECTRICALLY-CONDUCTIVE CONNECTIONS; STRUCTURAL ASSOCIATIONS OF A PLURALITY OF MUTUALLY-INSULATED ELECTRICAL CONNECTING ELEMENTS; COUPLING DEVICES; CURRENT COLLECTORS
- H01R4/00—Electrically-conductive connections between two or more conductive members in direct contact, i.e. touching one another; Means for effecting or maintaining such contact; Electrically-conductive connections having two or more spaced connecting locations for conductors and using contact members penetrating insulation
- H01R4/10—Electrically-conductive connections between two or more conductive members in direct contact, i.e. touching one another; Means for effecting or maintaining such contact; Electrically-conductive connections having two or more spaced connecting locations for conductors and using contact members penetrating insulation effected solely by twisting, wrapping, bending, crimping, or other permanent deformation
- H01R4/18—Electrically-conductive connections between two or more conductive members in direct contact, i.e. touching one another; Means for effecting or maintaining such contact; Electrically-conductive connections having two or more spaced connecting locations for conductors and using contact members penetrating insulation effected solely by twisting, wrapping, bending, crimping, or other permanent deformation by crimping
- H01R4/183—Electrically-conductive connections between two or more conductive members in direct contact, i.e. touching one another; Means for effecting or maintaining such contact; Electrically-conductive connections having two or more spaced connecting locations for conductors and using contact members penetrating insulation effected solely by twisting, wrapping, bending, crimping, or other permanent deformation by crimping for cylindrical elongated bodies, e.g. cables having circular cross-section
- H01R4/184—Electrically-conductive connections between two or more conductive members in direct contact, i.e. touching one another; Means for effecting or maintaining such contact; Electrically-conductive connections having two or more spaced connecting locations for conductors and using contact members penetrating insulation effected solely by twisting, wrapping, bending, crimping, or other permanent deformation by crimping for cylindrical elongated bodies, e.g. cables having circular cross-section comprising a U-shaped wire-receiving portion
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01R—ELECTRICALLY-CONDUCTIVE CONNECTIONS; STRUCTURAL ASSOCIATIONS OF A PLURALITY OF MUTUALLY-INSULATED ELECTRICAL CONNECTING ELEMENTS; COUPLING DEVICES; CURRENT COLLECTORS
- H01R43/00—Apparatus or processes specially adapted for manufacturing, assembling, maintaining, or repairing of line connectors or current collectors or for joining electric conductors
- H01R43/04—Apparatus or processes specially adapted for manufacturing, assembling, maintaining, or repairing of line connectors or current collectors or for joining electric conductors for forming connections by deformation, e.g. crimping tool
- H01R43/058—Crimping mandrels
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29K—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES B29B, B29C OR B29D, RELATING TO MOULDING MATERIALS OR TO MATERIALS FOR MOULDS, REINFORCEMENTS, FILLERS OR PREFORMED PARTS, e.g. INSERTS
- B29K2021/00—Use of unspecified rubbers as moulding material
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2333/00—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers
- C08J2333/18—Homopolymers or copolymers of nitriles
- C08J2333/20—Homopolymers or copolymers of acrylonitrile
Definitions
- Patented Nov. 7, 19 39 UNITED STATES MANUFACTURE or An'rmcrAL SILK- James J. Polak, Arnhem, and Johannes G. Weeldenburg, Ede, Netherlands, assignors to American Enka Corporation,
- the present invention has to do with a new and novel method for use in the manufacture of yarn or other materials of artificial origin and the products thereof.
- the present invention concerns a novel process for maintaining ideal spinning conditions in the manufacture of yarn of artificial origin.
- a cellulosic solution is prepared and expressed or extruded through minute openings into a coagulating or precipitating medium.
- This medium is usually either liquid or gaseous.
- cellulose is treated with caustic to form alkali cellulose, which, with carbon disulphide, produces a xanthate. This, in solution, produces a viscose spinning solution.
- spinnerets are made from gold, gold-palladium, gold-platinum, tantalum, et cetera.
- .Furthermore spinnerets are manufactured from precious and semi-precious stones, such as natural ruby, synthetic ruby, et cetera.
- Our improved procedures are applicable in the use of these various types or" spinnerets.
- the economic advantage of finding a simple, inexpensive method for keeping spinnerets operative during spinning is therefore apparent.
- other improved spinning conditions will be realized when following our procedures wherein we provide a solution for these problems in our present inventive concept.
- cation-active compounds are included either-in the spinning bath and/or the spinning solution, the clogging of spinneret openings is consider ably diminished or even prevented, and a very remarkable improvement of the spinning process per se -will result.
- cationactive aliphatic, carbocyclic or heterocyclic substances have been employed with signal success in actual practice.
- certain cation-active compounds are employed it is intended to mean that only those cation-active compounds are suitable which are sufliciently soluble and substantially stable in the spinning bath or the celluloslc solution or in both.
- Ca.- tion-active compounds are surface-active compounds which carry in the cation the group or radical which is responsible for the surface activity.
- anion-active compounds are surface-active compounds which carry in'the anion the group which is responsible for the surface activity.
- groups responsible for surface activity in this specification are called surface-active groups.
- Other 1d noticeable with the usual metal spinnerets, which groups or' ions which are inert in this respect will be called surface-inactive or innocuous.
- Surface activity as used herein is the property, among other physico-chemical characteristics, of reducing surface or interfacial tension.
- the extended chain remains with that part of the molecule bearing the positive charge, then it is said to be cationactive; whereas, on the other hand, if the long chain remains with that part of the molecule which bears a negative charge, it is said to be anion-active.
- Most of the usual surface-active substances are anion-active, with which substances the present invention is not concerned.
- a general structural formula for a compound of this type may represents the cation and A represents the anion.
- X represents a polyvalent atom, or a radical containing such an atom, capable of being linked to a negative atom or radical and at the same time to one or more other atoms or radicals.
- the letter 11 indicates the valence of the atom or radical X.
- the invention also contemplates the presence of more than one atom symbolized by x in the cation. In this event one or more of the X atoms may be linked to surface-active groups and to surface-inactive atoms or radicals as described herein.
- S designates the radical or radicals inducing cation-activity, which are linked directly to the polyvalent atom of X.
- S may include one or more of the same or different aliphatic, carbocyclic and heterocyclic radicals and the letter m is a positive whole number indicating the total number of such radicals.
- the radical or radicals S should be such that when linked radicals and/or hydrogen atoms.
- B may be hydrogen and/or one or more of the same or different aliphatic, carbocyclic or heterocyclic radical or radicals which are distinguished from those of S in that they do not induce surface-activity into the cation.
- the letter 11 is a positive whole number or zero and indicates the total number of such This letter 11. also indicates the number of valences of the atom of X whih remain available to be saturated by inactive atoms or radicals of the cation.
- the letter A represents an innocuous anion, i. e., an anion having no surface-activity or at least less surface activity than the cation.
- This anion is linked directly to the polyvalent atom of X and may be an atom or an inorganic or organic radical.
- the letter 0 is a whole number indicating the valence of the anion.
- the C outside of the bracket is a whole positive number indicating the number of cations linked to the anion. In the examples given herein C equals 0 and the sum of n and m equals y-l.
- the more important cation-active compounds which may be employed in accordance with the present invention are the bases or their salts, such as may be derived from pentavalent nitrogen, and further the sulphonium, phosphonium and arsonium, etc., bases and their salts.
- bases or their salts such as may be derived from pentavalent nitrogen, and further the sulphonium, phosphonium and arsonium, etc., bases and their salts.
- polyvalent atom of X in the foregoing formula is in these compounds nitrogen, sulphur, phosphorus and arsenic, etc., respectively.
- the quaternary ammonium compounds are examples of compounds containing such an atom, nitrogen being the polyvalent atom.
- the pyridonium or pyridinium compounds are examples of compounds in which the polyvalent atom, nitrogen,.is contained in a radical, the radical being the pyridine ring (C5H5N) having a valence of two.
- Other radicals containing the polyvalent atom may, of course, be used in place of the pyridine ring. 4
- the innocuous anion symbolized by A is the hydroxide, chloride, sulphate, bromide, iodide, acetate, etc.
- the groups inducing cation activity symbolized by Sm comprise extended chain-like structures, such as aliphatic hydrocarbon chains having six or more carbon atoms therein.
- the extended chain-like structures may be composed of two or more benzene nuclei or other cyclic radicals, either combineddirectly or, for example, through a carbon or nitrogen or other linkages, with or without aliphatic chains substituted for the-hydrogen in rings.
- bases derived from nitrogen and their salts for instance, certain pyridinium and other quaternary ammonium compounds, have been found to be particularly suitable.
- the former compounds may include pyridinium bases or salts having linked thereto extended aliphatic chains, containing, for example, six or more carbon atoms and preferably 12 to 20 carbon atoms.
- dodecyl, hexadecyl, octadecyl, or even a lower carbon chain such as decyl may be linked to the nitrogen atom in the bases or salts of pyridinium such as pyridinium hydroxide, pyridinium sulphate or bisulphate and pyridinium bromide.
- pyridinium such as pyridinium hydroxide, pyridinium sulphate or bisulphate and pyridinium bromide.
- Use may also be made of replacement or substitute compounds such as the analogous substitution products of pyridine known as 'picoline (C5H4N(CH3)), and quinoline (CoH'IN),
- the letter x represents the pyridine radical including the polyvending atom nitrogen and having a valence u of 2; S is the dcdecyl radical C12H25 connected directly to the polyvalent atom (nitrogen) 01 X, the letter m being 1.
- the innocuous anion A is the bisulphate radical (H304) connected directly to the polyvalent atom of X. The vale Cjust outside the b pound the'value of atom or radical R.
- the same innocuous anions and surface-active groups may be linked to the pentavalent nitrogen atom as are employed with the pyridinium compounds.
- X represents the atom
- the three are saturated in the pyrldinium compounds by (CHM are now saturated by alkyl, aryl or other. carbocyclic or heterocyclic groups and/or hydrogen atoms. .For instance, three methyl groups may be used to form trimethyl dodecyl ammonium bromide. The following is the structural formula of such a compound:
- the compound might contain more than one dodecyl radical or other radical capable of inducing the surface-activity of the cation.
- one or more of the methyl radicals in the above compound might be replaced by a including benzene trimethyl ammonium activity of the cation in the above compound;
- dcdecyl radical in which event the letter m would be 2 or more, depending upon how many methyl radicals were so replaced, and the letter n would be correspondingly decreased. If all the methyl radicals were replaced by radicals capable of inducing the surface activity of the cation, the letter 11. would, of course, become zero.
- the radicals capable of inducing the surface-activity oi the cation may include aromatic or other carbocyclic or heterocyclic radicals.
- the following compounds are examples of compounds containing such radicals groups in the cation: toluene azophenyl-trimethyl ammonium iodide, benzene azophenyl trimethyl ammonium iodide, diphenyl azophenyl methyl sulphate, isopropyl naphthyl trimethyl compounds the etc., represent the radicals inducing the surface- (S).
- a compound ot such as the dcdecyl Where the innocuous anion, is divalent, as in the case of a sulphate in which both hydrogens are replaced by surface-active cations, a compound ot, the following type may be used:
- the sulphur, phosphorus or arsenic must have linked directly thereto, an innocuous anion and at least one groupinducing surface activity in the cation. It is apparent that the sulphur being tetravalent, as distinguished from the pentavalent phosphorus and arsenic willhave less valances to be saturated than in, the case of phosphorus, arsenic and nitrogen.
- a sulphonium compound such as diethyl dcdecyl sulphonium hydroxide would correspond to triethyl dcdecyl phosphonium hydroxide, either of which might be used.
- trimethyl dodecyl phosphonium hydroxide and dipropyl dcdecyl sulphonium bromide may be employed.
- dodecyl pyridinium chloride dodecyl-triethyl ammonium iodide, octyl-triethyl ammonium iodide, decyl-triethyl ammonium iodide, dodecyl-triethyl ammonium iodide, hexadecyl-triethvl ammonium iodide, toluene azophenyl-trimethyl ammonium iodide, benzene azophenyl-trimethyl ammonium iodide, diphenyl-azophenyl-trimethyl ammonium methylsulphate, isopropyl-naphthyl-trimethyl ammonium iodide.
- diethyl-dodecyl sulphonium hydroxide triethyl-dodecyl phosphonium hydroxide, trimethyl-dodecyl pohsphonium iodide, trimethyl-dodecyi phosphonium bromide, dipropyl-dodecyl sulphonium bromide, etc.
- unsaturated as well as saturated aliphatic radicals may be used as the radical inducin surface-activity in the cation (S) or as the inactive radical (R).
- the cation-active compounds may be added directly to the viscose spinning baths, or may be mixed with the viscose solution prior to extrusion into the baths, or they may be employed simultaneously in both the bath and spinning solution. It is of course necessary to select a cation-active compound which is not adversely affected by the acid of the bath and is substantially stable when used therein, and/or one that is stable in viscose when used therein; Compounds which are-sumciently solu-. ble in dilute caustic soda or viscose to go into molecular solution in the viscose itself are particularly adapted to be added to the spinning solution.
- tetra-alkylammonium bases and salts and aryltrialkylammonium bases and salts are especially suited for this purpose because of their greater stability toward the alkali of the viscose.
- the compound when the compound is added to the spinning bath it ispreferred to use a compound that goes into molecular solution in the spinnine bath:
- Example 1 Ordinary viscose solution is made up, and spun or extruded through fine orifices in precious metal spinnerets into a well-known acid spinning bath, containing sulphuric acid, sodium sulphataammonium sulphate, and a small quantity of zinc sulphate. Such a bath, although widely known and used, is ordinarily troublesome since spinning taminated spinnerets, are common.. We add to the bath, however, a small quantity 0.04 per cent by weight) of dodecyl pyridinium bisulphate. A desirable range of this material is between one thousandth per cent'and eight hundredth per cent. Such a small addition eliminates most gold-palladium difficulties due to the conof the spinning irregularities and difflculties, and
- Example 2 An ordinary viscose solution is extruded through spinnerets into of the type mentioned in Example 1, but which contains a relatively larger amount of zinc sulphate, for example, five per cent of this salt. Ordinarily, under these conditions, the spinnerets become sufliciently contaminated in afew hours to deleteriously ailect spinning, as pointed out above. However, if 0.1 per cent by weight of dodecyl triethyl ammonium iodide is first added to the viscose solution, the tendency to clog the holes of the spinnerets will be greatly reduced.
- Example 3 An ordinary viscose solution is spun through gold-palladium spinnerets into a spinning bath containing, for example, in addition to the usual bath ingredients 5% zine sulphate; under these conditions the holes of the spinnerets will become contaminated within a few hours. 1f.however, 0.05% toluene azophenyl-trimethyl ammonium iodide is added to the viscose solution, there will be much less clogging of the spinneret holes.
- yarn we intend to cover filaments, threads, ribbons, foils, or other products usually produced by extrusion or spinning of a so-called cellulosic solution of artificial origin.
Description
Patented Nov. 7, 19 39 UNITED STATES MANUFACTURE or An'rmcrAL SILK- James J. Polak, Arnhem, and Johannes G. Weeldenburg, Ede, Netherlands, assignors to American Enka Corporation,
tion of Delaware No Drawing. Original application 1937, Serial No.
Enka, N. 0., a corpora January 25,
122,323. Divided and this application June 6, 1938, Serial No. 212,187.
Germany February is, 1935 3 Claims,
division of our appli- 122,323, filed January 25, 2,125,031 the latter being "not. application it a cation Serial Number 1937, now Patent No.
a continuation in part of our application Serial No. 51,332, filed November 23, 1935.
The present invention has to do with a new and novel method for use in the manufacture of yarn or other materials of artificial origin and the products thereof.
More specifically. the present invention concerns a novel process for maintaining ideal spinning conditions in the manufacture of yarn of artificial origin.
In the manufacture of artificial filaments, threads, yarns, ribbons and the like, a cellulosic solution is prepared and expressed or extruded through minute openings into a coagulating or precipitating medium. This medium is usually either liquid or gaseous.
In preparing the cellulosic spinning solutions referred to in the specific examples of the present case, cellulose is treated with caustic to form alkali cellulose, which, with carbon disulphide, produces a xanthate. This, in solution, produces a viscose spinning solution.
In the present specification we shall describe our invention with respect to a viscose process, but it must be understood that the underlying principle is broad, and that we do not wish to be limited to any specific, minute application of our concept.
in the commercial production of artificial yarn and analogous products, it is economically necessary, it possible, to provide for uninterrupted. spinning oi all filaments. Ordinarily the objections arising which occasion interruptions to the spinning or extruding step, are caused by the contamination of the spinnerets themselves. This fault can, we believe, be traced to the presence of suspensions, reaction products, and impurities of various kinds in the viscose solution or the spinning bath which tend to agglomerate or deposit on the spinneret and partially or entirely block the small orifices therein. These materials might include,' among others, precipitated cellulose, sulphur deposits, particles of and the like.
We have noted this phenomenon more espeerally used in such spinning baths.
Even if the deposit of material is lnsumcient to entirely clog the orifices, it acts to vary the.
resin, secondary reaction products,
thickness of the individual filaments, and consequently produces undesirable properties in the final product. Also, so-called spinning hooks tend to form at the obstructions, either in or around the orifices of the spinneret, which, when filaments are extruded therethrough, might cause a temporary interruption of the spinning of a filament at the orifice afiected, thus occasioning a tearing of the filament. These 'taults incuradditional expense due to the manip'ulation necessary to change spinnerets, the loss accruing from stopped production, and the increase. in lower quality yarns, for which yarns a lower price, only, may be asked.
The partial or total clogging-of orifices is spinnerets are made from gold, gold-palladium, gold-platinum, tantalum, et cetera. .Furthermore spinnerets are manufactured from precious and semi-precious stones, such as natural ruby, synthetic ruby, et cetera. Our improved procedures are applicable in the use of these various types or" spinnerets. The economic advantage of finding a simple, inexpensive method for keeping spinnerets operative during spinning is therefore apparent. As will be subsequently pointed out, other improved spinning conditions will be realized when following our procedures wherein we provide a solution for these problems in our present inventive concept. l 1
Briefly, we have discovered that it certain cation-active compounds are included either-in the spinning bath and/or the spinning solution, the clogging of spinneret openings is consider ably diminished or even prevented, and a very remarkable improvement of the spinning process per se -will result. More specifically, cationactive aliphatic, carbocyclic or heterocyclic substances have been employed with signal success in actual practice. By stating that certain cation-active compounds are employed it is intended to mean that only those cation-active compounds are suitable which are sufliciently soluble and substantially stable in the spinning bath or the celluloslc solution or in both. Ca.- tion-active compounds are surface-active compounds which carry in the cation the group or radical which is responsible for the surface activity. In contradistinction anion-active compounds are surface-active compounds which carry in'the anion the group which is responsible for the surface activity. Such groups responsible for surface activity in this specification are called surface-active groups. Other 1d noticeable with the usual metal spinnerets, which groups or' ions which are inert in this respect will be called surface-inactive or innocuous.
Surface activity as used herein is the property, among other physico-chemical characteristics, of reducing surface or interfacial tension.
As an additional advantage we have found that when such cation-active substances are added to the viscose spinning bath, either by direct addition or as a result of addition to the viscose solution, the colloidal sulphur therein tends to agglomerate, and is easily filtered off if desired. Together with the removal of the sulphur thus eftected, which in itself represents an impurity, other dissolved or suspended particles contaminating the spinning bath may be also precipitated and removed.
Surface activity depends upon the presence of one or more groups or radicals with long or ex-,
tended chain-like structures which includes extended aliphatic, carbocyclic and heterocyclic chains or combinations thereof. Compounds which contain a surface-active group show a tendency, according to the experiments and theory of Langmuir, to accumulate in the surface of interface of the solution and to assume an oriented position in which all of the extended chains lie parallel. Naturally, these substances can show this property only in so far as they are dissolved. When the molecules ionize, the surface activity may be induced by either the cation or the anion. This depends upon the position of the extended chain when the molecule ionizes. If, when the molecule ionizes, the extended chain remains with that part of the molecule bearing the positive charge, then it is said to be cationactive; whereas, on the other hand, if the long chain remains with that part of the molecule which bears a negative charge, it is said to be anion-active. Most of the usual surface-active substances are anion-active, with which substances the present invention is not concerned.
The compounds as exemplified below are illustrative of compounds which may be used in accordance with our invention. A general structural formula for a compound of this type may represents the cation and A represents the anion. X represents a polyvalent atom, or a radical containing such an atom, capable of being linked to a negative atom or radical and at the same time to one or more other atoms or radicals. The letter 11 indicates the valence of the atom or radical X. The invention also contemplates the presence of more than one atom symbolized by x in the cation. In this event one or more of the X atoms may be linked to surface-active groups and to surface-inactive atoms or radicals as described herein. S designates the radical or radicals inducing cation-activity, which are linked directly to the polyvalent atom of X. S may include one or more of the same or different aliphatic, carbocyclic and heterocyclic radicals and the letter m is a positive whole number indicating the total number of such radicals. The radical or radicals S should be such that when linked radicals and/or hydrogen atoms.
to X it or they will provide, in an ionizing solvent, a surface-active cation. B may be hydrogen and/or one or more of the same or different aliphatic, carbocyclic or heterocyclic radical or radicals which are distinguished from those of S in that they do not induce surface-activity into the cation. The letter 11 is a positive whole number or zero and indicates the total number of such This letter 11. also indicates the number of valences of the atom of X whih remain available to be saturated by inactive atoms or radicals of the cation.
The letter A represents an innocuous anion, i. e., an anion having no surface-activity or at least less surface activity than the cation. This anion is linked directly to the polyvalent atom of X and may be an atom or an inorganic or organic radical. The letter 0 is a whole number indicating the valence of the anion. The C outside of the bracket is a whole positive number indicating the number of cations linked to the anion. In the examples given herein C equals 0 and the sum of n and m equals y-l.
It is to be understood that all compounds of the above named general structure have the character of bases (wherein A would be a hydroxyl radical) or their salts, including acid salts.
The more important cation-active compounds which may be employed in accordance with the present invention are the bases or their salts, such as may be derived from pentavalent nitrogen, and further the sulphonium, phosphonium and arsonium, etc., bases and their salts. The
polyvalent atom of X in the foregoing formula is in these compounds nitrogen, sulphur, phosphorus and arsenic, etc., respectively. The quaternary ammonium compounds are examples of compounds containing such an atom, nitrogen being the polyvalent atom. Of these, the pyridonium or pyridinium compounds are examples of compounds in which the polyvalent atom, nitrogen,.is contained in a radical, the radical being the pyridine ring (C5H5N) having a valence of two. Other radicals containing the polyvalent atom may, of course, be used in place of the pyridine ring. 4
In the bases or their salts illustrated by the above formula the innocuous anion symbolized by A is the hydroxide, chloride, sulphate, bromide, iodide, acetate, etc. The groups inducing cation activity symbolized by Sm comprise extended chain-like structures, such as aliphatic hydrocarbon chains having six or more carbon atoms therein. Also, the extended chain-like structures may be composed of two or more benzene nuclei or other cyclic radicals, either combineddirectly or, for example, through a carbon or nitrogen or other linkages, with or without aliphatic chains substituted for the-hydrogen in rings.
Referring now in detail to specific examples of suitable compounds, bases derived from nitrogen and their salts, for instance, certain pyridinium and other quaternary ammonium compounds, have been found to be particularly suitable. The former compounds may include pyridinium bases or salts having linked thereto extended aliphatic chains, containing, for example, six or more carbon atoms and preferably 12 to 20 carbon atoms. Specifically, dodecyl, hexadecyl, octadecyl, or even a lower carbon chain such as decyl may be linked to the nitrogen atom in the bases or salts of pyridinium such as pyridinium hydroxide, pyridinium sulphate or bisulphate and pyridinium bromide. Use may also be made of replacement or substitute compounds such as the analogous substitution products of pyridine known as 'picoline (C5H4N(CH3)), and quinoline (CoH'IN),
GuHu hs oi In this compound the letter x represents the pyridine radical including the polyvaient atom nitrogen and having a valence u of 2; S is the dcdecyl radical C12H25 connected directly to the polyvalent atom (nitrogen) 01 X, the letter m being 1. The innocuous anion A is the bisulphate radical (H304) connected directly to the polyvalent atom of X. The vale Cjust outside the b pound the'value of atom or radical R.
If the other hydrogen of cc of A is l, and the letter acket is 1. In this com- 11 is 0, so there would be no the bisulphate were replacedby a second dodecyl-pyridinium group the-innocuous anion (S04) would have a valence of 2 and the letter outside the bracket would nitrogen, having five valances.
valences which ,50
' would be formed. In
become 2, indicating two dodecyl' pyridinium groups satisfying the two valances of the anion.
- In the bases or salts of picoline and quinoline the (C5H4N(CH:)) andthe (CrHwN) groups, respectively, would be the radical X containing the polyvalent atom, nitrogen.
In the other quaternary ammonium compounds the same innocuous anions and surface-active groups may be linked to the pentavalent nitrogen atom as are employed with the pyridinium compounds. In this case X represents the atom The three are saturated in the pyrldinium compounds by (CHM are now saturated by alkyl, aryl or other. carbocyclic or heterocyclic groups and/or hydrogen atoms. .For instance, three methyl groups may be used to form trimethyl dodecyl ammonium bromide. The following is the structural formula of such a compound:
(CHI) (CHI) In this.v case R would be the (CH3) radical, the letter n being 3, and A would be the bromine atom. a s
If two butyl radicals are substituted for two of the methyl radicals methyl dibutyl dcdecyl ammonium bromine this event the R would represent different radicals (CH: and C4H9), the total number of which would be 3.
Also the compound might contain more than one dodecyl radical or other radical capable of inducing the surface-activity of the cation. For example, one or more of the methyl radicals in the above compound might be replaced by a including benzene trimethyl ammonium activity of the cation in the above compound;
dcdecyl radical, in which event the letter m would be 2 or more, depending upon how many methyl radicals were so replaced, and the letter n would be correspondingly decreased. If all the methyl radicals were replaced by radicals capable of inducing the surface activity of the cation, the letter 11. would, of course, become zero.
As previously indicated the radicals capable of inducing the surface-activity oi the cation may include aromatic or other carbocyclic or heterocyclic radicals. The following compounds are examples of compounds containing such radicals groups in the cation: toluene azophenyl-trimethyl ammonium iodide, benzene azophenyl trimethyl ammonium iodide, diphenyl azophenyl methyl sulphate, isopropyl naphthyl trimethyl compounds the etc., represent the radicals inducing the surface- (S). These may be con nected to a polyvalent atom as in the ammonium salts referred to or to the polyvalent element of a radical; as in thecase of the pyridinium and similar compounds. It is obvious that both aliphatic radicals, for example, group, and carbocyclic or heterocyclic radicals, for example, such as the aromatic azo compounds referred to above, may be present in the compound as radicals inducing the surface activity oi the cation,
nuclei in the surface-active.
ammonium iodide. In such,
such as the dcdecyl Where the innocuous anion, is divalent, as in the case of a sulphate in which both hydrogens are replaced by surface-active cations, a compound ot, the following type may be used:
' HaCui di (dcdecyl-triethyl ammonium) sulphate.
By the same token that the cation-active pyridonium and other ammonium compounds are suitable in connection with the present invention, sulphonium, phosphonium and arsonium bases and their salts may also be used. of course, in
order for this to be true, the sulphur, phosphorus or arsenic must have linked directly thereto, an innocuous anion and at least one groupinducing surface activity in the cation. It is apparent that the sulphur being tetravalent, as distinguished from the pentavalent phosphorus and arsenic willhave less valances to be saturated than in, the case of phosphorus, arsenic and nitrogen. For example, a sulphonium compound such as diethyl dcdecyl sulphonium hydroxide would correspond to triethyl dcdecyl phosphonium hydroxide, either of which might be used. As further examples of these types of compounds, trimethyl dodecyl phosphonium hydroxide and dipropyl dcdecyl sulphonium bromide may be employed.
- It is also within the scope of our invention to use compounds in which the polyvalent atom of iris divalent or trivalent.- The prerequisites of such an element must be that; they will combine with an innocuous anion and a surface-activity in tion.
group inducing the ca The following are a number of compounds that may be usedin accordance'with our invention:
Octyl pyridinium iodide, dodecyl pyridinium bromide, hexadecyl pyridinium iodide, octadecyl pyridinium bromide, dodecyl pyridinium iodide,
dodecyl pyridinium chloride, dodecyl-triethyl ammonium iodide, octyl-triethyl ammonium iodide, decyl-triethyl ammonium iodide, dodecyl-triethyl ammonium iodide, hexadecyl-triethvl ammonium iodide, toluene azophenyl-trimethyl ammonium iodide, benzene azophenyl-trimethyl ammonium iodide, diphenyl-azophenyl-trimethyl ammonium methylsulphate, isopropyl-naphthyl-trimethyl ammonium iodide. diethyl-dodecyl sulphonium hydroxide, triethyl-dodecyl phosphonium hydroxide, trimethyl-dodecyl pohsphonium iodide, trimethyl-dodecyi phosphonium bromide, dipropyl-dodecyl sulphonium bromide, etc.
Also unsaturated as well as saturated aliphatic radicals may be used as the radical inducin surface-activity in the cation (S) or as the inactive radical (R).
As pointed out above, the cation-active compounds may be added directly to the viscose spinning baths, or may be mixed with the viscose solution prior to extrusion into the baths, or they may be employed simultaneously in both the bath and spinning solution. It is of course necessary to select a cation-active compound which is not adversely affected by the acid of the bath and is substantially stable when used therein, and/or one that is stable in viscose when used therein; Compounds which are-sumciently solu-. ble in dilute caustic soda or viscose to go into molecular solution in the viscose itself are particularly adapted to be added to the spinning solution. The tetra-alkylammonium bases and salts and aryltrialkylammonium bases and salts are especially suited for this purpose because of their greater stability toward the alkali of the viscose. when the compound is added to the spinning bath it ispreferred to use a compound that goes into molecular solution in the spinnine bath:
We herewith give three specific examples in order to more clearly disclose the present process:
Example 1 Ordinary viscose solution is made up, and spun or extruded through fine orifices in precious metal spinnerets into a well-known acid spinning bath, containing sulphuric acid, sodium sulphataammonium sulphate, and a small quantity of zinc sulphate. Such a bath, although widely known and used, is ordinarily troublesome since spinning taminated spinnerets, are common.. We add to the bath, however, a small quantity 0.04 per cent by weight) of dodecyl pyridinium bisulphate. A desirable range of this material is between one thousandth per cent'and eight hundredth per cent. Such a small addition eliminates most gold-palladium difficulties due to the conof the spinning irregularities and difflculties, and
enables a much longer spinning time free from the noted interruptions than has been heretofore possible.
Example 2 An ordinary viscose solution is extruded through spinnerets into of the type mentioned in Example 1, but which contains a relatively larger amount of zinc sulphate, for example, five per cent of this salt. Ordinarily, under these conditions, the spinnerets become sufliciently contaminated in afew hours to deleteriously ailect spinning, as pointed out above. However, if 0.1 per cent by weight of dodecyl triethyl ammonium iodide is first added to the viscose solution, the tendency to clog the holes of the spinnerets will be greatly reduced.
Example 3 An ordinary viscose solution is spun through gold-palladium spinnerets into a spinning bath containing, for example, in addition to the usual bath ingredients 5% zine sulphate; under these conditions the holes of the spinnerets will become contaminated within a few hours. 1f.however, 0.05% toluene azophenyl-trimethyl ammonium iodide is added to the viscose solution, there will be much less clogging of the spinneret holes.
We believe it remarkable that such small and relatively inexpensive amounts of substances may be employed, and still give such good results.
It must be understood that ii the addition is made to the spinning bath rather than to the spinning solution, as set forth in Example 1,
a spinning bath small further additions are necessary from time to time to replenish the compound lost or removed during the spinning operation.
By yarn" we intend to cover filaments, threads, ribbons, foils, or other products usually produced by extrusion or spinning of a so-called cellulosic solution of artificial origin.
Having now set forth our invention as required by the patent statutes, we desire to be limited only to the extent set forth in the following claims.
What we claim is:
" 1. In the manufacture of viscose yarn wherein a viscose solution is extruded through minute orifices into an acid precipitating bath to form filaments and the like therefrom, the step of extruding the viscose solution into the spinning bath containing dissolved therein a cation-active tetra-alkylammonium salt.
2. A method as defined in claim 1 in which an alkyl-triethyl ammonium sulphate is added to the spinning bath.
3. A method as defined in claim 1 in which dodecyl-triethyl ammonium sulphate is added to the spinning bath.
JAMES J. POLAK. JOHANNES G. WEELDENBURG.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEN37778D DE709497C (en) | 1935-02-16 | 1935-02-16 | Process for improving the spinning process in the manufacture of viscose rayon |
Publications (1)
Publication Number | Publication Date |
---|---|
US2179196A true US2179196A (en) | 1939-11-07 |
Family
ID=48586911
Family Applications (4)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US122323A Expired - Lifetime US2125031A (en) | 1935-02-16 | 1937-01-25 | Manufacture of artificial silk |
US212184A Expired - Lifetime US2179195A (en) | 1935-02-16 | 1938-06-06 | Manufacture of artificial silk |
US212185A Expired - Lifetime US2145527A (en) | 1935-02-16 | 1938-06-06 | Manufacture of artificial silk |
US212187A Expired - Lifetime US2179196A (en) | 1935-02-16 | 1938-06-06 | Manufacture of artificial silk |
Family Applications Before (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US122323A Expired - Lifetime US2125031A (en) | 1935-02-16 | 1937-01-25 | Manufacture of artificial silk |
US212184A Expired - Lifetime US2179195A (en) | 1935-02-16 | 1938-06-06 | Manufacture of artificial silk |
US212185A Expired - Lifetime US2145527A (en) | 1935-02-16 | 1938-06-06 | Manufacture of artificial silk |
Country Status (5)
Country | Link |
---|---|
US (4) | US2125031A (en) |
BE (2) | BE413164A (en) |
DE (2) | DE709497C (en) |
FR (2) | FR800404A (en) |
NL (1) | NL39956C (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2428387A (en) * | 1943-07-16 | 1947-10-07 | Rayonier Inc | Processing of refined chemical pulp into viscose by adding cation active sulphonium compounds |
US2514131A (en) * | 1945-11-08 | 1950-07-04 | Gen Aniline & Film Corp | Process of producing sheetings of a water-soluble film-forming material |
Families Citing this family (50)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2432085A (en) * | 1938-10-07 | 1947-12-09 | North American Rayon Corp | Viscose spinning solutions |
US2422021A (en) * | 1940-07-29 | 1947-06-10 | Ind Rayon Corp | Manufacture of thread or the like |
US2519227A (en) * | 1941-04-19 | 1950-08-15 | American Viscose Corp | Manufacture of yarns and the like |
US2423075A (en) * | 1942-09-01 | 1947-06-24 | Courtaulds Ltd | Manufacture of alginate threads |
GB568177A (en) * | 1943-02-19 | 1945-03-22 | Courtaulds Ltd | Improvements in and relating to the manufacture of threads, filaments, films and thelike from alginates |
US2462948A (en) * | 1943-05-19 | 1949-03-01 | Woonsocket Rayon Inc | Flotation process of clarifying regenerating baths |
BE456065A (en) * | 1943-06-29 | |||
US2481692A (en) * | 1944-04-12 | 1949-09-13 | Rayonier Inc | Cotton treated with a cation active amine |
US2451558A (en) * | 1944-11-06 | 1948-10-19 | Rayonier Inc | Chemically treated wood pulp and a method of producing a cellulosic product |
DE929064C (en) * | 1944-11-06 | 1955-06-20 | Rayonier Inc | Process for making viscose from wood pulp |
US2475128A (en) * | 1945-02-27 | 1949-07-05 | American Cyanamid Co | Treatment of spinnerettes |
FR957246A (en) * | 1946-12-14 | 1950-02-17 | ||
BE515618A (en) * | 1947-04-26 | |||
FR961353A (en) * | 1947-04-26 | 1950-05-11 | ||
BE487186A (en) * | 1948-02-09 | |||
BE487229A (en) * | 1948-02-18 | |||
NL83134C (en) * | 1954-05-12 | 1900-01-01 | ||
BE539699A (en) * | 1954-10-20 | |||
US2975020A (en) * | 1954-11-03 | 1961-03-14 | American Viscose Corp | Producing all skin viscose rayon |
US2852334A (en) * | 1954-11-03 | 1958-09-16 | American Viscose Corp | Method of producing viscose rayon |
US2971816A (en) * | 1954-11-03 | 1961-02-14 | American Viscose Corp | Process of producing viscose rayon |
US2976113A (en) * | 1954-11-03 | 1961-03-21 | American Viscose Corp | Process of producing viscose rayon |
US2906634A (en) * | 1954-11-03 | 1959-09-29 | American Viscose Corp | Method of producing viscose rayon |
US2975019A (en) * | 1954-11-03 | 1961-03-14 | American Viscose Corp | Producing all skin viscose rayon |
US2853360A (en) * | 1954-11-03 | 1958-09-23 | American Viscose Corp | Viscose spinning process |
US2845327A (en) * | 1954-11-03 | 1958-07-29 | American Viscose Corp | Method of producing viscose rayon |
US2888356A (en) * | 1954-11-03 | 1959-05-26 | American Viscose Corp | All skin viscose rayon |
US2849274A (en) * | 1954-11-03 | 1958-08-26 | American Viscose Corp | Producing all skin viscose rayon |
US2975021A (en) * | 1954-11-03 | 1961-03-14 | American Viscose Corp | Method of producing viscose rayon |
US2923637A (en) * | 1954-11-03 | 1960-02-02 | American Viscose Corp | Viscose solution |
US2890132A (en) * | 1954-11-03 | 1959-06-09 | John A Howsmon | Producing all skin viscose rayon |
US2898182A (en) * | 1954-12-30 | 1959-08-04 | American Viscose Corp | Method of preparing viscose rayon |
US2895787A (en) * | 1954-12-30 | 1959-07-21 | American Viscose Corp | Process of producing all skin rayon |
US2895788A (en) * | 1954-12-30 | 1959-07-21 | American Viscose Corp | Method of forming all skin viscose rayon |
US2941892A (en) * | 1955-01-31 | 1960-06-21 | Atlas Powder Co | Spinning of viscose |
BE548089A (en) * | 1955-06-27 | 1900-01-01 | ||
US2890130A (en) * | 1955-06-29 | 1959-06-09 | American Viscose Corp | Process of producing all skin rayon |
US2902381A (en) * | 1955-06-29 | 1959-09-01 | American Viscose Corp | Method of producing all skin rayon |
US2908582A (en) * | 1955-06-29 | 1959-10-13 | American Viscose Corp | Production of all skin rayon |
US2840448A (en) * | 1955-06-29 | 1958-06-24 | American Viscose Corp | Method of producing all skin rayon |
DE1082699B (en) * | 1955-10-26 | 1960-06-02 | Du Pont | Process for the production of structures from regenerated cellulose |
US2932578A (en) * | 1955-12-05 | 1960-04-12 | American Viscose Corp | Method of producing all skin rayon |
DE1144000B (en) * | 1958-12-13 | 1963-02-21 | Stockhausen & Cie Chem Fab | Process for coagulating viscose |
NL266943A (en) * | 1960-07-15 | |||
US3252816A (en) * | 1962-05-28 | 1966-05-24 | Allied Chem | Pigmented extrudable viscose solutions |
DE1517627B1 (en) * | 1962-08-31 | 1969-10-23 | Armour & Co | Process for the treatment of soiled filter fabrics in sewage treatment plants |
US3632300A (en) * | 1969-02-10 | 1972-01-04 | Ciba Geigy Corp | Polyacrylonitrile dyeing process |
CA954255A (en) * | 1970-09-11 | 1974-09-10 | Max Schwarz | Dyeing polyacrylonitrile or acrylonitrile-containing copolymer fibre material |
GB1387265A (en) * | 1971-07-23 | 1975-03-12 | Viscose Development Co Ltd | Ion exchange celluloses |
CN112338401B (en) * | 2020-11-27 | 2022-07-15 | 新乡市七星钎焊科技有限公司 | Welding rod cutting equipment with stoving function |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE539320C (en) * | 1928-06-01 | 1931-11-24 | I G Farbenindustrie Akt Ges | Process for the production of artificial textile products with a matt sheen |
DE570666C (en) * | 1929-01-25 | 1933-02-18 | I G Farbenindustrie Akt Ges | Process for the production of artificial structures with reduced gloss |
-
0
- BE BE419429D patent/BE419429A/xx unknown
-
1935
- 1935-02-16 DE DEN37778D patent/DE709497C/en not_active Expired
- 1935-06-07 NL NL73841A patent/NL39956C/xx active
-
1936
- 1936-01-07 BE BE413164A patent/BE413164A/fr unknown
- 1936-01-07 FR FR800404D patent/FR800404A/en not_active Expired
- 1936-02-01 DE DEN1951D patent/DE933050C/en not_active Expired
-
1937
- 1937-01-13 FR FR48093D patent/FR48093E/en not_active Expired
- 1937-01-25 US US122323A patent/US2125031A/en not_active Expired - Lifetime
-
1938
- 1938-06-06 US US212184A patent/US2179195A/en not_active Expired - Lifetime
- 1938-06-06 US US212185A patent/US2145527A/en not_active Expired - Lifetime
- 1938-06-06 US US212187A patent/US2179196A/en not_active Expired - Lifetime
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2428387A (en) * | 1943-07-16 | 1947-10-07 | Rayonier Inc | Processing of refined chemical pulp into viscose by adding cation active sulphonium compounds |
US2514131A (en) * | 1945-11-08 | 1950-07-04 | Gen Aniline & Film Corp | Process of producing sheetings of a water-soluble film-forming material |
Also Published As
Publication number | Publication date |
---|---|
FR48093E (en) | 1937-10-18 |
DE933050C (en) | 1955-09-15 |
DE709497C (en) | 1941-08-19 |
FR800404A (en) | 1936-07-04 |
US2125031A (en) | 1938-07-26 |
BE419429A (en) | 1900-01-01 |
US2145527A (en) | 1939-01-31 |
US2179195A (en) | 1939-11-07 |
NL39956C (en) | 1937-06-15 |
BE413164A (en) | 1936-02-29 |
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